Summerland Key, FL Homes for Sale under $500,000

/6
$499,000
- Land
22552 Jolly Roger Dr, Cudjoe Key, FL 33042

7049 sf Oceanfront Lot with beautiful views of Cudjoe Bay ! Build your dream home in Cudjoe Key ! Don't miss out on this great opportunity to build and live in one of the most desirable neighborhoods in the Keys !

Emily Lombard

Ocean Sotheby's International Realty

(786) 659-1030

22552 Jolly Roger Dr, Cudjoe Key, FL 33042
/6
$450,000
- Land
21865 Spain Blvd, Summerland Key, FL 33042

Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

Matthew Sheehan

Ocean Sotheby's International Realty

(305) 614-8634

21865 Spain Blvd, Summerland Key, FL 33042
/13
$475,000
- 4 Beds
- 3 Baths
- 1,620 Sq Ft
31052 Avenue H, Big Pine Key, FL 33043

Investment opportunity on 10,000 sq. ft. double lot near the Big Pine Community Park; the location offers easy access to US1, local shopping and more; Marathon and Key West are within easy reach. **DO NOT WALK THE PROPERTY WITHOUT APPOINTMENT** 2 units, 2 tenants; pets on premises. 1,060 sq. ft. mobile home has 3BD/2BA, exterior wood siding; interior has been updated. CBS garage has 560 sq. ft.

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(844) 542-1790

31052 Avenue H, Big Pine Key, FL 33043
/39
$495,000
- 1 Bed
- 1 Bath
- 754 Sq Ft
701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

Ian Calderwood

Bluescape Real Estate

(786) 551-4336

701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
/9
$472,000
- 2 Beds
- 1 Bath
- 460 Sq Ft
6 Beach Dr, Key West, FL 33040

Rare DOUBLE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot can be cleared providing huge wide water sunset views and the ability to add dockage with shallow boating access. Located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Repair trailer that is on site under the 50% rule, or build your dream home

Anneliese Dietrick

Coldwell Banker Schmitt Lower Keys (KW)

(786) 756-8747

6 Beach Dr, Key West, FL 33040
/9
$480,000
- Land
701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

Carmen Brake Waterfront Keys Realty Inc.

701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
/19
$475,000
- Land
701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
/18
$470,000
- Land
701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
/30
$485,000
- 2 Beds
- 1.5 Baths
- 604 Sq Ft
701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
/33
$435,000
- 1 Bed
- 1 Bath
- 528 Sq Ft
30170 Linda St, Big Pine Key, FL 33043

Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residence features a sturdy metal roof and is nestled on a generously sized, fully fenced lot, offering both comfort and privacy.Step inside to discover energy-efficient LED lighting throughout, complemented by an energy-efficient A/C system to keep you cool. The kitchen features a gas range, perfect for cooking

Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

30170 Linda St, Big Pine Key, FL 33043
/52
$425,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
/3
$449,000
- Land
- 0.34 Acre
- $1,303,896 per Acre
Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042

Oversized lot in gorgeous Sugarloaf Key with 15,000 Square feet ready for you to enter into the ROGO system. This sale comes with a ROGO Point Letter from Monroe County for 0 Disturbed Pine worth 24 points, giving you 44 points to enter into the ROGO system to build your dream home. Seller has done the Letter of Current Site Conditions with the County as well as engineering for a house, just

Pamela Stangler Expert Realty LLC

Lot 16 Date Palm Dr, Sugarloaf Key, FL 33042
/25
$474,000
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
27973 Snapper Ln, Little Torch Key, FL 33042

Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy

Bill Vaught (REO Vaught Realty LLC Vaught Realty

27973 Snapper Ln, Little Torch Key, FL 33042
/13
$435,000
- Land
24285 Caribbean Dr, Summerland Key, FL 33042

Purchase this deep draft canal front LOT in Summerland Key while the building permit is in-process for a 4 bedroom / 2 bath stilted single family residence (home is additional). The plans shown are for a 1920 sq ft' / 2 story Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the

Donna Pezzi Keller Williams Key West Compass Realty

24285 Caribbean Dr, Summerland Key, FL 33042
/35
$459,000
- 2 Beds
- 1 Bath
- 754 Sq Ft
31131 Avenue D, Big Pine Key, FL 33043

Make this Charming Keys cottage your little piece of paradise today. Complete Remodel 2 Bedroom 1 bathroom with a bonus office/guest room opening to a large screened patio and spacious back yard. This Home is a true Conch home Constructed with Miami Dade Pine originally built in Key West then moved to Big Pine to join the first few homes built on. the Island. Impact doors, new shutters, new roof,

Heather Mason Coastal Collection Real Estate Inc.

31131 Avenue D, Big Pine Key, FL 33043
/30
$470,000
- 1 Bed
- 1 Bath
- 748 Sq Ft
701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
/46
$497,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

Lanny Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
/15
$425,000
- 2 Beds
- 1 Bath
- 798 Sq Ft
69 Palm Dr, Key West, FL 33040

ROGO exempt! Opportunity to easily replace existing mobile with a hurricane-rated modular, wood frame or Concrete home in a relaxed Lower Keys community just 15 minutes from Key West. Located on a 60+ ft wide deep-water canal with a solid seawall that spans the width of the property, 35 feet--ideal for boating or fishing right from your backyard. Enjoy neighborhood amenities like tennis and

Natallie Liz Expert Realty LLC (HQ)

69 Palm Dr, Key West, FL 33040

Florida Monroe County Summerland Key

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In Summerland Key, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 18 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Summerland Key, FL and find the perfect fit for your homeownership goals.

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